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Toward molecular recognition: three-point halogen bonding in the solid state and in solution.

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This study introduces a robust three-point halogen bonding interaction, demonstrating significantly enhanced binding affinity compared to monodentate interactions. This advancement highlights halogen bonding

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Area of Science:

  • Supramolecular Chemistry
  • Chemical Crystallography
  • Organic Chemistry

Background:

  • Halogen bonding is a non-covalent interaction involving a halogen atom acting as a Lewis acid.
  • Multipoint interactions are crucial for molecular recognition and the formation of complex supramolecular structures.
  • Previous studies have explored halogen bonding, but optimizing multipoint interactions for enhanced binding affinity remains an active area of research.

Purpose of the Study:

  • To design and characterize a well-defined three-point halogen bonding interaction.
  • To investigate the influence of geometric complementarity on halogen bond strength.
  • To evaluate the potential of this interaction for solution-phase applications in molecular recognition.

Main Methods:

  • X-ray structural analyses of halogen bond donors and triamine acceptors.
  • Titration experiments to determine binding constants.
  • Comparative analysis of binding affinities with varying degrees of geometric fit.

Main Results:

  • Demonstrated an ideal geometric fit between tridentate halogen bond donors and a selected triamine.
  • Observed a binding constant approximately three orders of magnitude higher than with comparable monodentate amines.
  • Showcased significantly weaker binding with less geometrically complementary multidentate amines.

Conclusions:

  • A highly effective three-point halogen bonding interaction has been established.
  • Geometric complementarity is critical for maximizing binding affinity in multipoint halogen bonding.
  • This principle is expected to advance the application of halogen bonding in solution-phase molecular recognition.